有机习题 (31)
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Fukuyama Group - Group Meeting Problems
07/17/2011
1
42
3
M. Kawase et al., Org. Lett., 12, 4776 (2010)CO
2HMe
NPh
OTFAA (3 eq*)
AcOEt
0 °C to rt
87%
(* theoretically 2 eq)Ph
3PEtBr
n-BuLi, THF
–20 °C to rt;
AcOH, 80 °C
87%N
MeCF
3Me
PhO
OO
MePhIBF
4
+KOCEt
3 (3 eq)
THF
–78 °C to rt
74%[Fe
2(CO)
9]* (2 eq)
benzene
95 °C;
DBU (20 eq)
95 °C
51%OOO
* low yield under basic conditionH
H
E. M. Carreira et al., Angew. Chem. Int. Ed., 50, 2962 (2011)
Y. Landais et al., Org. Lett., 10, 4195 (2008)SiMe
3BocNHOH (2.5 eq)
NaIO
4 (2.5 eq)
MeOH/ H
2O
20 °C
52%OH
OsO
4, NMO
THF/ t-BuOH/ H
2O
20 °C
82%NH
HO
HO
OHNBoc
OHOHBoc
SmI
2
THF
–78 °C
60%*1
*1stereochemistry
not determinedJ. R. Alaniz et al., Angew. Chem. Int. Ed., 50, 7167 (2011)Dy(OTf)
3
CH
3CN, 80 °C
90%O
OHPhHN
PhNO
H
Fukuyama Group - Group Meeting Problems
07/24/2011
1
42
3OOMeOHHOH
HHBHT, PhH
235 ºC, 88%1) MeMgBr, CuBr•Me
2S
Me
2S, THF, –20 ºC
66%, 14:1 dr
2) TMSCHN
2
MeOH/PhH, rt, 93%BHT, PhH
120 ºC, 96%O
MeO
CO
2MeH
H
Me
M. L. Snapper et al., Org. Lett., 3, 2819 (2001)
O
N
2
ONO
NO
MeO
2CMeO
2C
H[Rh(OCOC
7H
15)
2]
2 (cat.)
DMAD
CH
2Cl
2
rt
70%
A. Padwa et al., Tetrahedron Lett., 34, 7853 (1993)
HO
LTA
CHCl
3
-40 °C
61%1) CrO
3
H
2SO
4/H
2O/acetone
rt, 96%
2) OsO
4, THF
rt, 79%
3) p-TsOH⋅H
2O
toluene, reflux
85%O
OOOTricyclic Compound
(C
17H
24O
3)
T. R. R. Pettus et al., J. Am. Chem. Soc., 133, 1603 (2011)
Y. Kita et al., Angew. Chem. Int. Ed., 44, 734 (2005)OOPhPhNIS (2.5 eq)
H
2O (5.0 eq)
MeCN
–40 to 0 °C
62%*
(*18% other diastereomixture)1) DDQ
MeCN-H
2O (10:1)
60 °C
58% (36% SM)
2) NaH
2PO
4, NaClO
2
2-methyl-2-butene
t-BuOH-H
2O (5:1), rt
92%CAN
MeCN-H
2O (1:1)
rt;
K
2CO
3
80%OO
I
O
Fukuyama Group - Group Meeting Problems
07/31/2011
1
42
3S. Blechert et al., J. Am. Chem. Soc., 126, 3534 (2004)N
HOHOH
NMe
OAc
N
HO
NMe
TFA, rt
61%*
* : DiastereomixtureN
MeON
2
O1) allyl alcohol
Rh
2(OAc)
4
CH
2Cl
2, rt
2) xylenes
reflux
85% (2 steps)3) H(OH)NMe⋅HCl
pyridine, MeOH
reflux
4) imidazole⋅HCl
EtOH, reflux
81% (2 steps)N
MeOHO
MeN
O
J. L. Wood et al., Tetrahedron, 66, 6647 (2010)
O
OOH
MeO
2CPd(PPh
3)
4, i-Pr
2NH
microwave
benzene
160 °C
60%1) DMP
CH
2Cl
2, rt
77%
2) cat. RuCl
3, NaIO
4
CCl
4-CH
3CN-H
2O
50%OO
OOO
CO
2MeHBr
J. Suffert et al., Angew. Chem. Int. Ed., 50, 3285 (2011)
TBSO
N
MeO
ISmI
2, HMPA
i-PrOH
THF, –35 °C
99%1) CsF, PhN(Tf)
2
DME
2) Pd(OAc)
2, PPh
3
HCO
2H, DMF
87% (2 steps)LDA
THF, –78 °C;
MeI
67%NMeO
Me
Y. Landais et al., Org. Lett., 10, 4441 (2008)
